


Sunny 100 Kinks Challenge

by WeirdItalianPlumber



Category: It's Always Sunny in Philadelphia
Genre: 100 Kinks Challenge, F/F, F/M, Hand Jobs, Kissing, Oral Sex, Tags will update as chapters do, Vibrators, i'm hoping to use several sunny ships, these tags make it look kinkier than it is
Language: English
Status: In-Progress
Published: 2018-07-04
Updated: 2018-09-16
Packaged: 2019-06-05 08:31:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,490
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15166751
Author URL: https://archiveofourown.org/users/WeirdItalianPlumber/pseuds/WeirdItalianPlumber
Summary: I'm trying a 100 Kinks Challenge from tumblr.Nothing super sexy. Some will be sweet, funny or weird. This will, hopefully, explore several Sunny ships.





	1. 85. Wake up in the middle of the night and have sex (then go back to sleep)- Chardee

**Author's Note:**

> Based off [the 100 kinks challenge](http://all-of-the-ships-are-sailing.tumblr.com/post/86601537822/100-kinks-nsfw). It's old, but I'm always behind on the cool trends.

“Goddammit, Charlie,” Dee snaps. “You’ve been doing this for an hour. Will you  _go the fuck_ to sleep?”

Charlie’s sleep-overs were nothing new to them, slowly becoming less and less sporadic. So, when he invited himself over to her apartment that evening, Dee didn’t think much about it. She had even grown used to his occasional bouts of insomnia, but his impatient groaning and tossing and turning were hitting her last nerve. Usually he’d give up and go watch tv. She’d find him in the morning passed out on her couch, his hand in a bag of chips. He didn’t seem to have any plans of leaving the room this time and it was becoming tempting to shove him to the floor.

“I can’t sleep, Dee,” he explains, adding on a sarcastic, “ _S_ _orry_.”

She sighs, looking at the clock. It’s becoming closer to being considered morning than night. She sits up, pulling her shirt off. Charlie flips on his side again, looking to see what the movement is. His eyes widen upon the discovery.

“Alright, let’s go,” she says. He looks confused- this is far from the sleeping she was demanding. “You get all sleepy and lazy after we bang,” Dee explains impatiently, “So pants off, let’s do this.”

He nods, not even trying to keep his eyes on her face, watching her bare chest as she moves.

His pajama pants, a pair of ugly long underwear, come off. Dee’s grateful that at least they’re convenient for this, considering he’s not wearing anything underneath. 

“Can I use, uh, your thing?” he asks awkwardly. Dee rolls her eyes, though she’s not actually irritated. He’s never liked the word.  _It’s called a vibrator,_ she’s tempted to correct, just to watch him squirm.

She opens her sidetable, pulling it out and passing it to him. He flips on the switch, watching the subtle changes in her body at the familiar sound. 

She instinctively pulls her bottoms off, ready to put it to use. Charlie places it between her legs, resting one hand on her knee, holding her in place. He slowly runs the object across her flesh as she reaches a hand to brush across her own breasts. He watches with fascination as she works herself. 

One hand stills with the vibrator, holding it in the spot that makes her grasp at the blankets. His other hand maintains a steady motion, running across his dick.

She’s breathing heavily now, with soft gasps and moans mixed in. It’s really turning him on, and he wants to be the cause of those sounds; he lets the toy drop on the mattress and positions his legs between hers. He grasps his dick and pushes in, fingers brushing her clit as their hips meet. Dee replaces his fingers with her own when he positions his arms on either side of her shoulders.

“Will you turn that thing off?” she scolds, “You’re gonna kill the batteries.”

He starts rolling his hips, bodies pressed closely together. “It’s fine, Dee,” he responds, beyond caring about anything other than what’s currently happening. “I’ll buy you new ones.” He considers where his money comes from. “Well, technically Frank will.”

Dee groans in disgust, Frank is the absolute last person she wants to think of right now. It doesn’t seem to bother Charlie, though; he continues thrusting without missing a beat, occasionally shifting into a slightly different angle. 

When his breaths become quick and shallow, she speeds up her own swirling, an attempt to finish first. The steady humming is a comfort that Steven is within arm’s reach, and that he’ll get her there, if necessary. Before she can think too much on it, Charlie gives one last good thrust hitting just the right spot. She feels his cock start twitching moments before her own body gives in.

" _Shit_ ,” he breathes in her ear after he comes, but his words are drowned out by her own shouts. Charlie presses a kiss to her jaw, the first kiss they’ve had all night Dee realizes, then rolls back to his spot in the bed. She switches off the toy and shoves in back in the drawer. Charlie grins at her, in that happy way that implies that he can’t believe Dee Reynolds, who’s been called a whore so many times, would even do that with him.

Dee pulls the blankets back over her, the cotton sheets cool on her flushed skin. She glances at the person lying next to her, intending to apologize for snapping earlier, that strange feeling of affection overpowering. She finds that he’s already sleeping peacefully.

She returns his smile from earlier, not caring that he won’t see it. Maybe there are benefits to these sleepless nights. 

**Notes for the Chapter:**

> -I don't mean the whore part as an insult  
> -Dee does get back to sleep, too.


	2. 96. While one of them is on the phone- Chardee

**Summary for the Chapter:**

> Dee doesn't want to take this phone call. Charlie distracts her.

**Notes for the Chapter:**

> I was hoping to start mixing up some ships, but this one just called to me. Yet, it's still nothing spectacular. 
> 
> Warning- If you're really sensitive to incestuous type stuff, proceed with caution. Nothing sexual happens between the twins, nor do they think about each other in that way. Dennis just hears some stuff, but he doesn't know what it is. It's supposed to be funny. If the gang has seen his sex tapes, then he can (sort of) hear it live.

Dee’s phone rings when she’s getting ready for the day.  

“It’s Dennis,” Charlie yells from the couch. Of course that asshole has to call when she’s busy. As if she doesn’t have anything going on in life. His face staring at her from the screen furthers her irritation, the unflattering picture of him no help in easing her anger.  

She grabs her phone off the coffee table, answering with a sharp “what?” and striding back into her bedroom. 

Charlie mutes the tv and follows her. She’s standing in front of the closet, in a tank top and underwear, phone to her ear. He observes for a moment before approaching her.  

“Mmmm, you smell good,” he murmurs, face buried in her neck.  

“Yeah. That’s what happens when you shower,” Dee hisses back.  

“Hey! I do that, too,” Charlie argues defensively. 

She worries for a second that Dennis can hear. It’s clear that he has no intentions of shutting up soon, bitching about the idiots at his boring office job. Dee really can’t bring herself to care. This could be a great distraction. She allows Charlie to continue messily sucking on her neck in a way he probably thinks is sexy. It’s working for her, though.  

Knowing how much this would piss her asshole brother off definitely helps.  

She turns and steps around his legs, slowly rubbing against his thigh. His fingers slip into the waistband of her underwear, softly rubbing at the sensitive skin. Dee runs her fingers through his hair, lightly grasping a handful. Dee walks backwards leading them anywhere to take this further. She bumps into her dresser and decides to go with it. Placing a hand over his, they push her underwear to the floor and she climbs onto the dresser, knocking things to the side.  

She anticipates his pants to fall to the floor next. Working himself hard, then sliding in and banging her until the wooden furniture slams against the wall.  

Instead, Charlie drops to his knees, splaying her thighs while he stares up at her. Dee wants to command him to get the fuck to work already. The tantalizing mixture of cool air and his warm breath only making her more desperate for his tongue. His head dips and he starts slowly, teasing and tasting. Dee lets her head fall backward, resting against the wall as her eyes slip closed.  

He picks up speed, sucking and licking. Dee throws her legs over his shoulders, locking her ankles, angling for more pressure. He seems to be enjoying himself almost as much as she is. When she starts to squirm, he reaches out to grip her ass, never ceasing in his efforts. He pulls back slightly, inhaling more air before intensely diving right back in.  

The combination of Charlie’s soft hair tickling her thighs and his tongue slurping her like his first beer in days, is enough to get her  _there._  Dee comes with a sharp yelp, knees falling wide and legs dangling on either side of Charlie’s shoulders. Dennis stops in the middle of his prattling that she hadn’t even been listening to. “What the hell was that?” he demands.  

Dee releases her bottom lip from between her teeth. “Nothing,” she lies, “Just saw a rat. In the bar.” He simply grunts an “oh” and goes back to talking about himself. Charlie’s mouth continues moving, gradually easing to a stop. Dee glares at Charlie, who looks amused at her situation.  

She jerks her chin up, instructing him to stand. He rises to kiss her, mouth hot and wet. She uses her free hand to rub the obvious tent in his jeans. His deep moans are muffled in her mouth, never reaching the phone’s close mouthpiece. Dee’s quick, smoothly pulling down Charlie’s zipper and grasping his hard cock. She strokes rough and fast, his expression turning to desperation as his hips press forwards, leaning with one hand onto the wall behind her. He comes with a rough grunt, shooting hard into her fist. 

“Okay,” Dennis demands impatiently, “Something’s going on.” 

Dee grabs a box of Kleenex, balancing the phone between her shoulder and ear, while using a tissue to wipe her hand. “It’s nothing,” she says dismissively, “Something just…spilled.” Dee grins at her own joke, passing the box to Charlie.  

It must be believable. Dennis laughs, a little too cruelly Dee notes, “Sounds like Charlie has a mess to clean up.”  

She laughs at his choice of words. “Yeah,” she says, hopping off the dresser and patting Charlie on the shoulder. “He does.”  

**Notes for the Chapter:**

> -Does Dee's apt even have a closet? I don't remember. I'm gave her one for this.  
> Fun fact: I lived in an old farm house in elementary and my room didn't have a closet.
> 
> -Dennis will probably be bouncing back and forth between Philly and ND in this, depending on what works.


	3. 9. First time- Cindee

**Summary for the Chapter:**

> It's not her first time ever, but it is Dee's first time with a woman.

**Notes for the Chapter:**

> There's not much to say. Set during 13x01.

Dee’s not sure how they made it from the club to her apartment, but they’re here now and neither are wasting any time.  

They had gone out for a girls’ night- the kind Dee had dreamed of. Fancy high calorie drinks, dancing, all at a bar with beautiful people and low lights.  

Cindy is gorgeous, and she’s here in Dee’s apartment, and she’s as into Dee as Dee is into her.  

She’s never been with a woman before, Dee considers, a little sadly. 40 years old and never once. She’s kissed women before, plenty of times, but it’s never gone anywhere. It’s not that she hasn’t imagined it- those nights alone, pretending that her dildo sliding in and out of her pussy, guided by her own hand was not some guy’s dick, but a hot chick with a strap on. That her own long, thin fingers rubbing at her clit belonged to some nameless woman she met at a bar.  

But this is real, Cindy is real, and she’s everything Dee’s wished that she, herself, could be- beautiful, and smart, and a whole list of other things. Cindy pulls her dress over her head, and Dee finds herself staring. Cindy grins, snapping Dee back to reality, “Your turn.” 

Dee reaches for the hem of her own dress, it seems tighter and more difficult to pull off than when she put it on earlier that evening, but that might just be the eagerness. When she emerges from the fabric she feels momentarily self-conscious at Cindy’s wide eyed gaze of amazement. 

“Wait,” Dee says, when Cindy’s arms disappear behind her back, reaching for her bra clasp. She feels embarrassed asking, but she can’t stop herself, “Can I do it?”  

Cindy looks a little surprised, but nods, arms moving away. Dee steps forward, feeling her body heat, as she effortlessly unclasps the garment. Cindy moves to let the straps fall off her shoulders, as they share intense eye contact and shallow breaths.  

Dee’s hands move to cup Cindy’s breasts, thumbs gently stroking her smooth skin. Cindy’s eyes drift shut at the touch. When her eyes open, she looks at Dee’s chest then moves to mouth at the sensitive skin. Dee takes the initiative to remove her own bra, craving more of that contact. Once she’s fully exposed, Cindy’s mouth moves lower, swirling her tongue around each nipple then lifting her head to watch Dee.  

Cindy moves forward pressing Dee against the wall, always the natural leader. Cindy’s hand rests on the waistband of her own panties. “Should I?” She asks, knowing goddamn well the answer is  _yes._  

Dee nods. “Fuck, yes,” she breathes, placing a hand on Cindy’s other hip, helping her push the fabric to the floor.  

“You’re so pretty,” Cindy says, hand gently resting against Dee’s cheek, then leaning in for a kiss.  

Dee giggles nervously. She’s not used to being called pretty. Not used to believing it. “Shut up,” she responds, “You are.”  

“I know,” Cindy agrees with a sexy confidence. “We’re two hot ladies enjoying each others hot bodies.”  Her hands travel down Dee’s sides, caressing the outline of her breasts, finally landing on her hips. Cindy’s fingers skim the last bit of clothing between them, pushing Dee’s panties to the floor.  

Dee dips her head down, kissing and sucking at the soft skin in the crook of Cindy’s neck. The mixture of perfume and sweat turning her on more. Her hands leave Cindy’s long hair, moving to feel her soft curves.  

Cindy repositions a leg between both of Dee’s, shifting them apart. Dee moans lightly at the change, slowly, instinctively rubbing her need against Cindy’s thigh. They continue at the easy rhythm. Cindy replaces her knee with her hand, rubbing at the other woman’s wet folds, savoring the sounds she makes. She watches as Dee gasps then squeezes her eyes shut, as Cindy pumps two fingers in her.  

Dee comes clenching around Cindy’s fingers, their bare breasts pressed together.  

She moves forward, pushing Cindy away, walking her backwards until she falls onto the couch. Dee drops to her knees, making eye contact as her tongue flicks out licking at her own lips. She kisses the inside of Cindy’s thighs, teasing, knowing how badly she must want this. Her mouth slowly travels up towards her body, then gently and eagerly parting her.  

Dee rests a hand on Cindy’s hip, concentrating on her task. Cindy reaches to intertwine their fingers, squeezing Dee’s hand as she squirms under her tongue. She continues, alternating between licking and sucking, enjoying every second.  

Dee knows what she must need now, what she would want in this position; she pulls out of Cindy’s grip, placing her hand to rest on her own head. Cindy pulls at Dee's hair, then threads her fingers through it. Dee places her newly freed hand under her chin, and slides two fingers into her companion, curling them as her tongue circles the other woman’s clit. Cindy comes soon after, making what Dee’s pretty sure is the hottest sounds she’s ever heard.  

Cindy tugs at Dee’s wrist, urging her up next to her on the couch. Dee complies, sinking back into the cushions feeling unusually content.  

Dee chuckles awkwardly, breaking the silence, “Can you imagine what the guys would say if they found out about this?” She would never tell them. As much as she would love to brag about this, she knows they would only ruin it.  

Cindy turns to her, sighing tiredly. “Dee, you’ve got to stop caring about what those idiots think. You’re better than that,” Cindy encourages her. Before Dee can respond, Cindy gives her a quick, soft kiss adding. “You’ve got me, now.”  

**Notes for the Chapter:**

> This was originally going to be Dee/some random woman, but 13x01 aired, and I had to change it.  
> Cindy is encouraging Dee to be more confident/independent in general at the end. Not saying she needs to shift dependence on someone else.  
> Is it okay to say underwear in smut? Because the other term feels weird to me.


End file.
